Chapter 17 of 20 · Structure and Argument
1 The bottom line
Open on a moment or a question that makes the reader need the next line, and write that opening last, once you know what the piece is. Readers decide in seconds, and a weak opening loses them before the good part.
2 Key takeaways
- Drop the reader into a moment, not the backstory. Readers have endless alternatives and give you seconds.
Harlan Coben51:20 opens I Will Find You with "I am serving the fifth year of a life sentence for murdering my own child. Spoiler alert, I didn't do it."
Garry Tan27:10 tells founders a web page has "five or 10 seconds or less to prove your value."
- Make the first line plant a question the reader needs answered. Curiosity pulls people to the second line.
Jason Fried40:28 opened a letter with "Something happened to business software." It is a statement, yet readers ask what happened.
- Give the reader a reason to care within the first paragraphs. Readers start out assuming the piece is not for them.
Nat Eliason37:00 put a $100 million loss of other people's money into the first two paragraphs of his prologue.
- Write the opening last, when you know what the piece is. Only a finished draft shows what the opening must set up.
Henrik Karlsson11:16 moved a throwaway mid-essay line, "no, I just like Alice", to the top of Looking for Alice, and the piece cohered.
Gillian Flynn1:07:36 wrote the Gone Girl opening about the shape of the wife's head after the book was done, to set theme and mood.
- When readers leave, blame the opening and spend your hours there. Most readers never reach a late payoff.
Scott Dikkers27:06 saw in The Onion's heat maps that 85% of readers never read the full article.
Michael Pollan46:20 rewrote the Botany of Desire introduction 25 to 30 times.
Do not start where when the earth cooled. Start with the action right now.
Lee Child, Jack Reacher
2.1 Set the promise before you draft
The opening keeps a promise, so decide the promise first, even if the opening words come later.
- Decide why someone would click before you write.
Johnny Harris10:15 treats this as the first job.
- He drafts seven or more titles, usually starting with how or why, and checks comparable videos on tools like 1 of 10 or ViewStats.
- He tries two or three packagings. The package fixes the promise to answer, not the story itself.
- For the Saudi Arabia video he set the headline "why is Saudi Arabia building a futuristic city in the desert" before filming.
- Pick the title first, then find the content that earns it.
Mark Manson38:22 studied direct-sales copywriting and applied it to headlines.
- Once he knew a killer title could carry a post, he began with the title and then found the research to justify it.
Sam Parr41:05 asks what the YouTube title would be. He does it less for clicks than because it frames the piece and shows him the hook.- From 2012 to early 2015 Manson's blog grew from about 100,000 monthly readers to about 2.5 million.
- Make the promise strong, because a weak one means nobody reads far enough to find the payoff.
Nat Eliason32:15, citing Brandon Sanderson, splits a story into promise, progress and payoff.
- A mediocre payoff or a slow middle can be forgiven. Open with something that makes readers need to know what happens.
- Atlas Shrugged has flawed dialogue, but "Who is John Galt?" carries 350,000 words.
Sam Parr40:25 says lifting click-through from 1% to 10% is a far bigger gain than polishing the body. At 1%, only one of 100 people who see a headline opens it.
2.2 Draft first, then write the opening
The opening is easiest to write once the piece exists and you can see what it needs to set up.
- Write the opening after the rest of the draft. Four writers say it.
Flynn1:07:36 finds the first sentence intimidating, so she pictures herself diving in a few paragraphs along. Then she goes back to write the opening.
Karlsson11:16 writes the beginning and ending last. A paragraph he knows is an opening makes him pretentious and tense, and he can burn three hours on one that does not survive a reread.- Once the essay exists, the opening is usually already somewhere in the middle, so he moves it to the top
Karlsson11:16. - Flynn's husband thinks the Sharp Objects opening is her weakest and says she should have gone back and fixed it
Flynn1:07:36.
- Let the finished draft tell you what the opening is for.
David Grann53:01 wrote the final opening of The Wager once he had a full manuscript. Only then did he see the book is about a fight over the truth, so he opened with "The only impartial witness was the sun."
Jimmy Soni1:13:02 sent his editor an introduction written before the rest of the book. She told him to get it out of her face, because he did not yet know the dimensions of the story.- Soni says an intro works as a user's guide, so write it when you can tell readers where to go and what to notice
Soni1:13:02. - Grann's opening line tormented him for years before the manuscript was whole
Grann53:01.
- Turn the main pieces of your draft into questions, then fold them into the first sentence.
Michael Dean40:43 says not to write the hook directly.
- Draft the piece, ask which questions matter, then compress them into the subtext of the opening sentence. The questions then work as the outline of the opening section.
- Orwell's "I was hated by large numbers of people" raises three questions.
- Charlie Bleecker's memoir hook about stealing a whole bottle of Adderall took about 17 rewrites.
- Rework it many times, because people judge the whole piece from it.
Pollan46:20 says "Very important decisions about your book will be made based on the introduction and nothing else."
- A good introduction has an origin story, teases the questions, previews the book and keeps something back.
- He worked on the Botany of Desire introduction with his editor Ann Godoff and friend Paul Tough.
2.3 Drop the reader into a moment
Start where something is happening now, and explain the past later, if at all.
- Skip the biography and start in the action.
Lee Child44:46 says beginners think they must explain where a character grew up before the story starts. His rule is in medias res: open on something intriguing, explain later.
David Gelb20:51 took the cold open from James Bond films: start in the action, run the credits, then begin the story. The hook does not have to fit the rest of the episode.- For the Stan Lee film he opened with where the idea of Spider-Man came from, not where Lee was born. He gives the hook a minute or two
Gelb20:51. - The Chef's Table episode on Massimo Bottura opens with the earthquake that destroyed the Parmesan wheels
Gelb20:51.
- Open with your most intense scene, tell part of it, then step back.
Tucker Max1:30:52 calls this the one memoir structure that always works.
- Start in the middle of a very intense scene, leave it unfinished, then tell the full story. Don't open with "I was born a young boy on a ranch".
- Phil Klay's Redeployment opens with "We shot dogs". Max read the sample, bought the book and canceled a meeting to keep going.
Tim Ferriss57:36 opens a chapter of The 4-Hour Body with himself at Shoreline Amphitheater after his third pizza, reaching into a bowl of chocolate-covered almonds while two friends stare in disgust.
- Use the first line to say what kind of story this is.
Coben51:20 avoids having a character walk in, sit down and notice the flowers. He starts in the middle and promises the story in the first sentence.
Harris18:32 likes first lines that throw people into action. His Mormon video begins "It started with the murder of their prophet in Illinois", not "I want to tell you the story of the Mormons".
David Perell35:46 notes Mitch Albom learned from his uncle Eddie's war stories that you drop in with "So there we were" and leave out the argument over exact years.
- Recreate a camera move in a few sentences.
Steven Johnson1:11:30 opened the preface of Infernal Machine on a bustling NYPD room in 1915. He pulled the camera out, down the stairs, to a briefcase in a doorway with a clock ticking inside. He never said to imagine a movie.
Richard Powers56:32 borrows the wide shot, then the mid shot, then the close one. His wide openings set the size of the canvas and earn him the right to tell a small story inside it.- Johnson's paragraph is five or six sentences. It had to be memorable enough that readers tolerate a long journey before returning to it
Johnson1:11:30. - Powers opens The Overstory with "First there was nothing, then there was everything". The line came from a poet friend's last words on her deathbed
Powers56:32.
2.4 Plant a question or raise the stakes
Withhold one thing so the reader has to keep going to find it.
- Write a first line that gives the reader something new and raises a question.
Neil Strauss27:04 loves lines that make you lean in, such as the clocks striking thirteen, the mother who died today or maybe yesterday, and ships carrying every man's wish.- A statement can do it as well as a question. Fried writes that line first, and when it comes out right he knows the whole piece will work
Fried40:28.
- Withhold one small piece of information.
Patrick Radden Keefe17:50 says readers are jaded.
- He opened a story on Chapo Guzman's Sinaloa cartel at Amsterdam's Schiphol airport, with a travel-loving assassin who posted vacation photos and was arrested there.
- A reader expecting arid Mexican landscapes wonders how they get back. It subverts the expectation of a cartel story right away.
- Lead with a jarring person or a claim that could be false.
Susan Orlean10:19 wants a lead that confuses the reader just enough. She describes John Laroche as sharply handsome, then adds that he is missing all his front teeth.- When the subject is obscure, lead with a person, because "people are very interested in people"
Orlean9:53.
The Cultural Tutor1:12:28 makes the first line falsifiable, so a scrolling reader stops to see if it's true.- His thread opened with the claim that Hokusai's Great Wave is not a painting but a woodblock print, and it drove much of his early engagement
The Cultural Tutor1:12:28.
- Put the highest stakes in the opening.
Eliason37:00 added personal stakes beside the money, a crying baby and an angry wife, then jumped back nine months so the reader wonders how he got from excitement to disaster.
Grann48:02 finds prologues the hardest part. For The Lost City of Z he put himself lost in the jungle, a scene from late in the book, and wove in the stakes and themes.- Grann's prologue runs about 800 to 1,000 words and says "trust me, there is a reason I am telling this"
Grann48:02.
2.5 Give the reader a reason to care
Readers owe you nothing, so say why this matters or tell a story that makes it matter.
- Assume nobody cares, then earn it.
Strauss35:29 assumes readers do not care about him, his life or his ideas. His test is whether you want to read the passage aloud to a friend.
Steven Pinker1:55 says to tell the audience what problem you solve and why it is significant before presenting findings.- At TED, a molecular biologist launched into experiments in lab jargon and lost the whole room in about four seconds
Pinker1:55.
- Give a story its reason for being told before you tell it.
Tom Segura49:11 asks what his way in is: why am I telling this story?- For his Subway story he opened by saying he never thought he'd play arenas, since booking the Subway campaign was the highlight of his career. The audience is engaged before the story starts
Segura49:11. - The same story told as "one time I almost was the spokesman for Subway" gets a shrug
Segura49:11.
- Frame the idea instead of chasing a clickbait hook.
Shaan Puri20:17 says a hook is about the words in the first line, and a frame is about the idea.
- A frame makes the idea relevant by connecting it to things that seem unrelated. He could present one Hasan Minhaj lesson as a comedy tip or as how not to embarrass yourself at a dinner party intro.
- His Clubhouse thread, told as a screenplay ("you're the founder of Clubhouse, you're winning"), reached about 20 million readers.
- Open dry or analytical material with a story, yours or someone else's.
Ben Thompson3:03 opened a piece on the Disney Charter standoff with the first commercial satellite and the rocket launch, then moved into arcane carriage disputes.
Morgan Housel5:16 prefers one vivid, specific story to a general claim, as long as the hook stays honest and does not become hyperbole.
Michael Mauboussin1:05:52 opened The Success Equation with how he got his job, a random event that set up the theme of luck.- Housel prefers "the Vanderbilts had the equivalent of $300 billion and within 60 years it was almost all gone" to "rich families often go broke"
Housel5:16. - Readers still call Mauboussin "the trashcan guy" because of the story that opens Think Twice
Mauboussin1:05:52.
2.6 Keep the line crisp and test it
Once you have the moment or the question, say it plainly, in the voice of the whole piece.
- Do not oversell the opening scene.
Strauss40:47 says people who start with a story overwrite it, adding adjectives until the essence is lost. He plays moments down and saves the fine details for when the reader is inside the house.
Anne Lamott32:10 gives a book three pages in a bookstore. She wants clean, pleasing sentences that are not showy, and loses interest if it tries to sound literary.- Strauss mocks the fake version: a crisp, sharp morning in Knoxville, where I glanced at my watch
Strauss40:47.
- Let the idea arrive one piece at a time.
- Strauss says one of the biggest mistakes is cramming the whole thought into the opening. Lean back and draw readers in step by step
Strauss37:30. - His teaser gives one fact per line: a call from the FBI, a request to train agents, then the word seduction
Strauss37:30.
- Strauss says one of the biggest mistakes is cramming the whole thought into the opening. Lean back and draw readers in step by step
- Test how the first line sounds.
Robert Macfarlane10:12 spends longer on first lines than on whole chapters. He checks rhythm, alliteration and internal rhyme so the reader's inner ear wakes up in the first seconds.- He opens The Wild Places with "The wind was rising so I went to the wood"
Macfarlane10:12.
- Use the first line to set a bar for every later line.
Tom Junod54:44 does not write an opening to hook a reader. He writes one that lets him go on.
- Once the first sentence is right, hold every later sentence to its standard.
- "He departs from this earth like an arrow" made the hair stand up on his arms and set the standard for The Falling Man.
- Design the whole way in, not only the first sentence.
Dikkers26:36 thinks in a sequence of hooks.
- The sequence is headline, photo, caption, pull quote, first paragraph. Each needs its own small laugh, and a block of gray copy with no headline is a brick wall nobody climbs.
Sam Parr41:28 rejects "the article was too long". He says the slope wasn't slippery enough, so craft the first lines hard.
2.7 What the books say
Minto gives a simple shape for an opening: tell a short story the reader already knows, so the reader asks the very question your main point answers.
- Open with a story the reader already knows, then lead to the question.
Barbara Minto, The Minto Pyramid Principle
- State a Situation nobody will argue with, set in a time and place. Then add the Complication that happened next, and name the Question it raises.
- Answer the Question with your main point. This puts you and the reader in the same place, so the conclusion feels natural.
- Do not open by announcing a purpose and a list of topics.
Barbara Minto, The Minto Pyramid Principle
- A board memo that opened with a purpose and five topics became clear when rewritten. It said a new October organization freed the Board for policy, the Board still dwelt on short-term problems, so it should hand day-to-day matters to an Executive Committee.
- Open each section with a mini story or a backward reference.
Barbara Minto, The Minto Pyramid Principle
- Say what the section says, not what it does. Either tell a short Situation, Complication, Question that leads to the section's point, or pick up a key word from the part just finished.
- In the Ritz-Ryan report, each section picked up a key idea from the one before, such as the full-time Chief Executive.
2.8 Where writers disagree
| Opening first | Opening last | Draft, then rewrite | |
|---|---|---|---|
| Who | Fried, Junod, McCormick | Flynn, Karlsson, Grann | Strauss |
| Why it works | Settles framing; rest follows | Draft shows what it must set up | Finds voice, then fits final piece |
| Risk | May not match where piece went | Blank start feels intimidating | Extra rewrite pass |
The best order, and the best kind of opening, depends on the piece and the reader.
- Write the opening first or last. Most of the writers above say last, but some start there.
Fried40:28 writes his opening line first, and
Junod54:44 needs a first sentence that lets him go on.
Packy McCormick3:52 spends most of his effort on the first few paragraphs, like picking a line before skiing a fresh run. Once the framing is settled, the rest follows.
Strauss42:15 polishes the first chapter early as a container for his rough draft. He expects it to move, because the best opening usually reflects where the book really went.- A fair compromise: draft an opening to find your voice, then rewrite it when the piece is done.
- How much to polish page one.
Mitch Albom20:59 rewrote the Tuesdays with Morrie opening about 20 times. His editor told him a book buyer will give you a few pages, so he aimed to hook readers within ten pages.
Macfarlane10:12 rewrites first lines hundreds of times, and
Pollan46:20 25 to 30 times. A web page gets far less patience 
Tan27:10.
- Open with a story or with the answer.

Lenny Rachitsky16:41 finds introductions usually far too long. He puts the answer first and the supporting detail below, for readers who want more.
Keefe20:50 writes for readers who want to be seduced by narrative. He wants the first few paragraphs to intrigue them enough to stay.- Lenny still keeps a checklist atop every draft with the prompt "what is a good story I can start this thing with"

Rachitsky29:34.
- Promise big or promise small.
Eliason32:15 says a strong promise is what gets anyone to your payoff.
Karlsson31:20 says a big promise turns writing into labour, because you keep checking whether you delivered. A small puzzling observation lets him wander and end up overdelivering.- His piece on the childhoods of exceptional people promised a catalogue from 40 books and was painful to write. His piece on unpublished books promised only a little thinking
Karlsson31:20.
- Do not use the same kind of opening every time.
Atul Gawande22:14 warns that readers are biased against the predictable as well as the boring. If every chapter opens in the emergency room, the mechanics show.- He sometimes opens with a surprising idea and sometimes with a scene, and says it took him a long time to learn
Gawande22:14.
Sources
- How to Write Thrilling Stories (Gillian Flynn Interview) ·
How I Write - How to Write a Novel (For Beginners) — Harlan Coben Interview ·
How I Write - The Deepest Conversation You’ll Ever Watch About Writing (Shafak & Macfarlane Interview) ·
How I Write - The 11 Tricks Behind Funny Storytelling (Scott Dikkers Interview) ·
How I Write - Harvard Professor Teaches Writing (Michael Pollan Interview) ·
How I Write - How to Make Your Writing Funny (Tom Segura Interview) ·
How I Write - How to Become a Better Writer (Anne Lamott Interview) ·
How I Write - The Secret to Great Stories (David Gelb Interview) ·
How I Write - New Yorker Writer Teaches the Craft of Writing (Patrick Radden Keefe Interview) ·
How I Write - Learn to Write Page-Turners in 63 Minutes (Lee Child Interview) ·
How I Write - The Truth About Writing Nobody Wants to Say (Tom Junod Interview) ·
How I Write - I Interviewed 40 Writers in 2025 (Here's What I Learned) ·
How I Write - How to Use Writing to Improve Your Thinking — Atul Gawande ·
How I Write - Meet The Writer Behind Killers of the Flower Moon ·
How I Write - Award-Winning Author Reveals Her Writing Process (Susan Orlean Interview) ·
How I Write - Why Selfish Writing Is Better Writing (Morgan Housel Interview) ·
How I Write - How to Write Exceptionally Well (Mitch Albom Interview) ·
How I Write - One of The World's Most Under-Rated Writers — Henrik Karlsson ·
How I Write - Cambridge Professor: Why All Writing Sounds the Same Now (Robert Macfarlane) ·
How I Write - Harvard Professor Explains The Rules of Writing (Steven Pinker Interview) ·
How I Write - How He Wrote Forrest Gump (And Many Other Movies) ·
How I Write - A New Way to Teach Writing — Meet Michael Dean ·
How I Write - Johnny Harris Reveals How He Writes YouTube Videos ·
How I Write - 171 Years of Writing Knowledge in 90 Minutes ·
How I Write - The Secret To A New York Times Best Seller – Tucker Max ·
How I Write - How to Become a Master Storyteller (Richard Powers Interview) ·
How I Write - How He Started the Paid Newsletter Trend — Ben Thompson ·
How I Write - Writing Formulas Everybody Should Know (Mark Forsyth Interview) ·
How I Write - Learn Copywriting in 76 Minutes – Harry Dry ·
How I Write - NYU Professor: Writing Masterclass in 84 Minutes – Scott Galloway ·
How I Write - How to Tell Captivating Stories in 103 Minutes – Nat Eliason ·
How I Write - Seinfeld’s Timeless Lessons on Creativity and Consistency ·
How I Write - The New Rules of Business Communication — Jason Fried ·
How I Write - How to Be Great? Just Be Good, Repeatably | Steph Smith | How I Write Podcast ·
How I Write - The FBI Called This Writer About Seduction Training — Neil Strauss ·
How I Write - How to Tell an Unforgettable Story (The Shaan Puri Interview) ·
How I Write - Write Like Wall Street’s Best — Michael Mauboussin ·
How I Write - Packy McCormick: A Tactical Masterclass in Online Writing ·
How I Write - The Expert Behind Google’s NotebookLM AI Writing Tool ·
How I Write - Why Writing Is the Key to Your Thinking | Tim Ferriss ·
How I Write - The Writing Secrets of a World Class YouTuber – Ali Abdaal ·
How I Write - Y Combinator CEO: The Key To Writing For Startups & Entrepreneurs | Garry Tan | How I Write Podcast ·
How I Write - How to Become a Bestselling Author (Mark Manson Interview) ·
How I Write - How Lenny Rachitsky Got 531,000 Substack Subscribers | How I Write Podcast ·
How I Write - Inside the Mind of a Newsletter Mogul (Sam Parr Interview) ·
How I Write - Marc Andreessen: Blogposts, Tweetstorms, and Manifestos ·
How I Write - How to Write Like An Athlete | with Jimmy Soni | How I Write Podcast ·
How I Write - The Cultural Tutor: From McDonald's to Twitter Stardom ·
How I Write - The Minto Pyramid Principle: Logic in Writing, Thinking and Problem Solving · Books
Part of Structure and Argument in the growth library.